Middlesboro, KY Homes

• 

  

  

  /13

  $140,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  413 S 26th St, Middlesboro, KY 40965

  This beautiful 2 bed 1 bath with beautiful hardwood floors, sits only minutes away from downtown Middlesboro and the Cumberland Gap National Park. This home has had some great improvements such as a new roof and new windows installed. don't miss your opportunity to call this your own.

  

  Brad Cawood

  Turn Key Realty

  413 S 26th St, Middlesboro, KY 40965
• 

  

  

  /5

  $1,200 Per Month

  • 2 Beds
  • 1 Bath
  • 680 Sq Ft
  • Townhouse for Rent

  801 Winchester Ave, Middlesboro, KY 40965

  Property Id: 1779914Located 4.5 miles from LMU Campus. This property boast down town walking, restaurants, quick trials response.

  801 Winchester Ave, Middlesboro, KY 40965
• 

  

  

  /11

  $152,500

  Sold Oct 10, 2025

  102 Stone Creek Dr, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $160/SF
  • 9 Days On Market

  Current Estimated Value $146,269

  Last Listing Agent Misti McGrath Realty Group

  102 Stone Creek Dr, Middlesboro, KY 40965
• 

  

  

  /33

  Not Listed For Sale

  2817 Ky 441, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft
  • Built 2020

  2817 Ky 441, Middlesboro, KY 40965

  Last Sold Summary

  • 72 Days On Market
• 

  

  

  /18

  $93,500

  $32K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,426 Sq Ft

  123 Cawood Ln, Middlesboro, KY 40965

  Large Price Reduction!! Charming 2 bedroom, 1.5 bath home situated on a beautiful, quiet lot with plenty of potential and possibilities! This property features an extra-large carport, storage shed, and inviting front porch perfect for enjoying peaceful mornings or evenings outdoors. The large backyard offers plenty of space for entertaining, gardening, or relaxing, while the enclosed back

  

  Dustin Daniels

  Mountain Realty

  123 Cawood Ln, Middlesboro, KY 40965
• 

  

  /15

  $1,400 Per Month

  • 3 Beds
  • 3 Baths
  • 1,200 Sq Ft
  • House for Rent

  565 S 43rd St, Middlesboro, KY 40965

  Property Id: 2705023Welcome to your new home at 565 S. 43rd St. in Middlesboro, KY! This charming 3 bed, 3 bath single-family home features modern amenities such as a washer/dryer, fenced yard, and central heat pump. Perfect for pet lovers with cats and small dogs allowed. Don't miss out on this gem!For more information Contact Kevin Carroll

  565 S 43rd St, Middlesboro, KY 40965
• 

  /2

  $170,000

  Sold Jun 04, 2026

  4605 W Cumberland Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1995

  Last Sold Summary

  • 3% Above List Price
  • $161/SF
  • 37 Days On Market

  Current Estimated Value $147,953

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  4605 W Cumberland Ave, Middlesboro, KY 40965
• 

  

  /8

  Est $75,468

  Not Listed For Sale

  108 S 8th St, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Built 1935

  108 S 8th St, Middlesboro, KY 40965

  Last Sold Summary

  • 7 Days On Market
• 

  

  /20

  $399,000

  • 3 Beds
  • 3 Baths
  • 3,397 Sq Ft

  103 Kingsbury Woods Rd, Middlesboro, KY 40965

  Rare opportunity to own a premier golf course property on Hole #2 at the Middlesboro Golf Course—one of only four homes situated directly on the course. Perfectly positioned on a generous 0.67-acre lot, this spacious residence offers a grand total living space, including a finished basement, providing plenty of room to live, entertain, and relax. With three bedrooms and three full baths, the home

  Anthony Gigilo ListWithFreedom.com

  103 Kingsbury Woods Rd, Middlesboro, KY 40965
• 

  

  /9

  $900 Per Month

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft
  • Condo for Rent

  561 S 43rd St, Middlesboro, KY 40965

  Property Id: 1567269Welcome to your new home at 561 S. 43rd St. in Middlesboro, KY! This charming 2 bed/2 bath condo is perfect for anyone looking for a cozy and convenient living space. With amenities such as a dishwasher, washer/dryer, central heat/AC, and more, you'll feel right at home. Enjoy the nearby parks and on-site laundry facilities. Pets are welcome (cats/small dogs) and

  561 S 43rd St, Middlesboro, KY 40965
• 

  

  /30

  $202,000

  Sold Feb 17, 2026

  140 Chasteen Dr, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1954

  Last Sold Summary

  • 6% Below List Price
  • $112/SF
  • 4 Days On Market

  Current Estimated Value $210,422

  Last Listing Agent Kevin Bisceglia Coldwell Banker Bisceglia Realty & Auction Co

  140 Chasteen Dr, Middlesboro, KY 40965
• 

  

  /13

  Est $168,598

  Not Listed For Sale

  514 Avondale Ave, Middlesboro, KY 40965

  • 4 Beds
  • 3 Baths
  • 2,627 Sq Ft
  • Built 1985

  514 Avondale Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 34 Days On Market
• 

  

  /30

  $125,000

  Pending

  • 4 Beds
  • 2 Baths
  • 2,592 Sq Ft

  316 Exeter Ave, Middlesboro, KY 40965

  Looking for an older home to bring back to life. This home has all the old wood trim. big rooms with fireplaces in most of the rooms, this home comes with an extra building lot and a garage/ carport also. Call Now!!

  Steve Mason REMAX PROFESSIONAL'S

  316 Exeter Ave, Middlesboro, KY 40965
• 

  

  /9

  $1,150 Per Month

  • 3 Beds
  • 1 Bath
  • Condo for Rent

  210 S 10th St Unit 210, Middlesboro, KY 40965

  Property Id: 2602777Welcome to this charming 3 bedroom, 1 bathroom unit in Middlesboro, KY. This multi-family property features a refrigerator, oven, central heat pump, balcony, washer/dryer hookups, and a driveway. Enjoy the convenience of being near by parks, grocery, and retail shopping while living in this lovely home. 5 minutes from LMU main campus. Rent for $1150 with outside

  210 S 10th St Unit 210, Middlesboro, KY 40965
• 

  

  /15

  $105,000

  Sold Apr 17, 2026

  921 Winchester Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1940

  Last Sold Summary

  • 9% Below List Price
  • $78/SF
  • 98 Days On Market

  Current Estimated Value $108,450

  Last Listing Agent Virginia Wilder Century 21 Virginia Wilder Real Estate

  921 Winchester Ave, Middlesboro, KY 40965
• 

  

  /20

  Est $139,213

  Not Listed For Sale

  316 Avondale Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,456 Sq Ft
  • Built 1997

  316 Avondale Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 55 Days On Market
• 

  

  /14

  $50,000

  • 3 Beds
  • 1 Bath
  • 728 Sq Ft

  105 Nutwood Rd, Middlesboro, KY 40965

  3 bed, 1 bath fixer-upper in Middlesboro, KY! Great investment opportunity—flip, rent, or make it your own. City water/sewer (per public record). Priced for potential—bring your ideas!

  Megan Stanaford Black Diamond Realty

  105 Nutwood Rd, Middlesboro, KY 40965
• 

  

  /13

  $1,275 Per Month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  1027 Chichester Ave Unit 1027 B, Middlesboro, KY 40965

  Property Id: 25754562 bed / 1 bath pet friendly. Large yard. Minutes from LMU campuses. Credit check, background check, eviction check required per adult tenant. Pet considered on individual basis with non refundable pet deposit. Tenant pays utilities, electricity, water (and garbage), internet. Landlord will take care of yard. $375 nonrefundable pet deposit per pet (pet

  1027 Chichester Ave Unit 1027 B, Middlesboro, KY 40965
• 

  /2

  $167,000

  Sold Sep 15, 2025

  414 SE North 24th St, Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1972

  Last Sold Summary

  • 10% Below List Price
  • $104/SF
  • 2 Days On Market

  Current Estimated Value $157,318

  Last Listing Agent Beth Combs Turn Key Realty

  414 SE North 24th St, Middlesboro, KY 40965
• 

  

  /28

  Est $94,333

  Not Listed For Sale

  333 Avondale Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 770 Sq Ft
  • Built 1930

  333 Avondale Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 10 Days On Market
• 

  

  /28

  $59,900

  • Land
  • 4.24 Acres
  • $14,127 per Acre

  1197 Beans Fork Rd, Middlesboro, KY 40965

  Opportunity awaits on this 4.24-acre tract offering a peaceful setting with endless potential. The property was previously improved with a home that has recently been lost to fire, presenting a unique chance to start fresh and bring your vision to life. With utilities previously in place (buyer to verify), this parcel may offer a head start for rebuilding, whether you're considering a custom

  SARAH RICHARDS RE/MAX Preferred Group

  1197 Beans Fork Rd, Middlesboro, KY 40965
• 

  /2

  $1,000 Per Month

  • Studio
  • 1 Bath
  • 680 Sq Ft
  • Townhouse for Rent

  302 S 27th St, Middlesboro, KY 40965

  Property Id: 2704830This charming townhouse in Middlesboro, KY is perfect for a single individual. With 1 bathroom, washer/dryer in unit, and designated parking space, this cozy home is pet-friendly for cats and small dogs. Enjoy amenities such as dishwasher, dryer, freezer, oven, and refrigerator. Built in 1978, this property also features central heating, laminate flooring, and a heat

  302 S 27th St, Middlesboro, KY 40965
• 

  

  /17

  $160,000

  Sold Jul 03, 2025

  524 E Lothbury Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $200/SF
  • 5 Days On Market

  Current Estimated Value $150,674

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  524 E Lothbury Ave, Middlesboro, KY 40965
• 

  

  /17

  Est $76,405

  Not Listed For Sale

  205 S 9th St, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1997

  205 S 9th St, Middlesboro, KY 40965

  Last Sold Summary

  • 11 Days On Market
• 

  

  /5

  $855,000

  • 2 Beds
  • 2 Baths
  • 15,119 Sq Ft

  725 19th St, Middlesboro, KY 40965

  Prime Multifamily Investment Opportunity Presenting a well-established commercial apartment building in the heart of Middlesboro, Kentucky. Built in 1990, this single-story property offers approximately 15,225 square feet of space ideally suited for residential rental units, providing stable cash flow in a convenient location. Strategically positioned on N 19th Street, the building benefits from

  Beth Combs Turn Key Realty

  725 19th St, Middlesboro, KY 40965
• 

  /2

  $10,000

  Sold Oct 17, 2025

  Lot #1 Bellwood Rd, Middlesboro, KY 40965

  • Land
  • 12,196 Sq Ft
  • $35,714 per Acre

  Last Sold Summary

  • 50% Below List Price
  • 42 Days On Market

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  Lot #1 Bellwood Rd, Middlesboro, KY 40965
• 

  

  /42

  Est $121,371

  Not Listed For Sale

  215 Armadale Ave, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1985

  215 Armadale Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 40 Days On Market
• 

  

  /4

  $159,000

  $5K PRICE DROP

  • 700 Sq Ft

  1801 Exeter Ave, Middlesboro, KY 40965

  2 HOMES with one FULLY remodeled home in back 2 bedroom 1 bath Cute as a button! Home on corner lot needs work but would be a very smart investment. With access to ATV friendly roads, close to stores and hospital.1801 Exeter and 1801 1/2 Exeter

  Misti McGrath Realty Group

  1801 Exeter Ave, Middlesboro, KY 40965
• 

  

  /20

  $148,400

  Sold Jul 16, 2025

  112 Parker Ln, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,439 Sq Ft
  • Built 2011

  Last Sold Summary

  • 2% Above List Price
  • $103/SF
  • 174 Days On Market

  Current Estimated Value $170,959

  Last Listing Agent David Gambrell Coldwell Banker Bisceglia Realty & Auction Co

  112 Parker Ln, Middlesboro, KY 40965
• 

  

  /45

  Est $330,853

  Not Listed For Sale

  915 E Lothbury Ave, Middlesboro, KY 40965

  • 3 Beds
  • 4 Baths
  • 2,349 Sq Ft
  • Built 1945

  915 E Lothbury Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 23 Days On Market
• 

  

  /5

  $30,000

  • Land
  • 1.26 Acres
  • $23,810 per Acre

  0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965

  LOCATION!! LOCATION!! Ready to build your dream home. Property is located minutes from Middlesboro. Wooded lot with electric and water available. Close to shopping, restaurants and hospitals. Minutes from LMU main campus. Buyer to verify acres!

  Sharon Teaney Century 21 Virginia Wilder Real Estate

  0 Lots 12 & 13 Sams Mountain Rd Unit 1328410, Middlesboro, KY 40965
• 

  

  /24

  $196,000

  Sold Nov 26, 2025

  515 N 25th St, Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 2,000 Sq Ft
  • Built 1918

  Last Sold Summary

  • 2% Below List Price
  • $98/SF
  • 117 Days On Market

  Current Estimated Value $183,752

  Last Listing Agent Misti McGrath Realty Group

  515 N 25th St, Middlesboro, KY 40965
• 

  

  /19

  Est $176,881

  Not Listed For Sale

  225 N 10th St, Middlesboro, KY 40965

  • 3 Beds
  • 1.5 Baths
  • 1,014 Sq Ft
  • Built 1930

  225 N 10th St, Middlesboro, KY 40965

  Last Sold Summary

  • 90 Days On Market
• 

  /2

  $50,000

  • Land
  • 16,639 Sq Ft
  • $130,890 per Acre

  0000 Edgewood Rd, Middlesboro, KY 40965

  Lot on Edgewood road, can be purchased with 205 N 20th Street Middlesboro KY; former duplex was removed and now vacant land. City utilities available.

  Megan Stanaford Black Diamond Realty

  0000 Edgewood Rd, Middlesboro, KY 40965
• 

  /2

  $13,000

  Sold Sep 25, 2025

  Lot #6 Bellwood Rd, Middlesboro, KY 40965

  • Land
  • 17,859 Sq Ft
  • $31,707 per Acre

  Last Sold Summary

  • 35% Below List Price
  • 14 Days On Market

  Last Listing Agent Sheila Durham Coldwell Banker Bisceglia Realty & Auction Co

  Lot #6 Bellwood Rd, Middlesboro, KY 40965
• 

  

  /34

  Est $197,066

  Not Listed For Sale

  215 S 15th St, Middlesboro, KY 40965

  • 4 Beds
  • 2.5 Baths
  • 1,824 Sq Ft
  • Built 1980

  215 S 15th St, Middlesboro, KY 40965

  Last Sold Summary

  • 35 Days On Market
• 

  /2

  $79,000

  $20K PRICE DROP Pending

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  923 Winchester Ave, Middlesboro, KY 40965

  This cozy apartment with 1 bedroom and 1 bathroom has an office attached and storage room with garage door, city water, public sewer, paved driveway, corner level lot, natural gas available and high speed internet available, close to hospital.

  Virginia Wilder Century 21 Virginia Wilder Real Estate

  923 Winchester Ave, Middlesboro, KY 40965
• 

  

  /18

  $95,000

  Sold May 22, 2026

  1009 E Cumberland Ave, Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Built 1935

  Last Sold Summary

  • 17% Below List Price
  • $112/SF
  • 12 Days On Market

  Current Estimated Value $108,938

  Last Listing Agent Michael Hensley REMAX PROFESSIONAL'S

  1009 E Cumberland Ave, Middlesboro, KY 40965
• 

  

  /11

  Est $180,051

  Not Listed For Sale

  403 E Lothbury Ave, Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 3,360 Sq Ft
  • Built 1972

  403 E Lothbury Ave, Middlesboro, KY 40965

  Last Sold Summary

  • 10 Days On Market
• 

  

  /18

  $135,000

  Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,963 Sq Ft

  901 Exeter Ave, Middlesboro, KY 40965

  Hey Neighbors! If you've been looking for a solid property with room to build some serious sweat equity, you'll want to take a look at this one. Sitting on a spacious corner lot inside the Middlesboro city limits, this 1.5-story brick veneer home offers a massive 1,963 square feet of living space and sits on over half an acre 0.539 acres per (Bell County PVA). With a potential of 4 bedrooms, 2

  Russell Tribell Fathom Realty KY LLC

  901 Exeter Ave, Middlesboro, KY 40965

Showing Results 1 - 40, Page 1 of 18